Unlike many of his fellow NASCAR competetor’s, Michael Waltrip didn’t start racing until he was in his teens primarily racing go-karts through out the Midwest. After moving to late model stock cars, his career took off in 1981, when he captured the Mini-Modified division track championship at Kentucky Motor Speedway. A year later, Michael entered the Goody's Dash Series, where he won the series championship in 1983 and was voted the circuit's most popular driver in 1983 and 1984.

Micahel made his Cup debut in 1985 in the Coca-Cola 600 at Charlotte. He finished 28th in that race and finishing 57th in the series standings after just five starts. Driving for Dick Bahre in 1986, Michael finished second in the Cup rookie of the year race to Alan Kulwicki on the strength of a pair of 11th-place finishes at Martinsville and Pocono.

In 1988, Michael moved into the Busch Series, making five starts for his brother Darrell's fledgling team. It didn't take long for Michael to make an impact by taking the checkered flag at Dover in just his fourth start. Michael's most memorable Busch Series effort came in 1993 at Bristol. After taking the checkered flag, Michael made a "Polish victory lap" in honor of Kulwicki, who had lost his life in a plane crash on his way to that weekend's events. What's more, he proposed to his wife Buffy in Victory Lane that day.

While Michael had always been a competitive driver through the '80s and '90s -- even winning The Winston in 1996 – however, he had the dubious honor of having the longest active streak of Cup point-paying starts without a victory. Finally that 463-race streak ended at the best place it could, the 2001 Daytona 500. Later that same season, he finished second behind teammate Dale Earnhardt Jr. in the Pepsi 400, also at Daytona.